1022 Fleming Street, Key West, FL 33040
$1,999,990
Property Type:
Residential
Bedrooms:
4
Baths:
2
Square Footage:
2,016
Lot Size (sq. ft.):
2,724
Status:
Active
Current Price:
$1,999,990
List Date:
9/09/2025
Last Modified:
10/31/2025
Description
Invest in Key West with this legal Duplex! Step into a piece of Key West history with this fully renovated, light-filled historic home in the heart of Old Town. Blending old-world charm with modern updates, this property offers easy living and generates income. Whether you're looking for a smart investment, a vacation getaway, or a new primary residence, this property is ready for you. Live in one unit and rent the other, or enjoy the entire home for yourself! There is an interior staircase to enter the upstairs unit.
Each spacious level features 2 bedrooms, 1 bathroom, a full kitchen with stainless steel appliances, laundry, and an open-concept living/kitchen/dining area. The lower unit opens to a deck and pool—perfect for relaxing and entertaining. The upper unit boasts abundant natural light and a large wraparound porch, ideal for enjoying the tropical surroundings. Both units come fully furnished, and the upstairs unit has a long-term tenant in place, ensuring immediate rental income.
Located in a prime spot close to the Old Seaport, top restaurants, and bars, but in a quieter neighborhood, this home is your ticket to island living in paradise!
More Information MLS# 616423
Contract Information
Listing Board: Key West Association
As is Rght to Inspct: Yes
Potential Short Sale: No
Bank Owned: No
Species List: No
Current Price: $1,999,990
Listing Date: 2025-09-07
List Price: $1,999,990
Location, Tax & Legal
KW Neighborhood: Old Town-N of Truman
City: KEY WEST
Mile Marker: 1
Marathon Neighborhood: N/A
Side: Median
Flood Zone: AE
Alternate Key #: 1007617
Handicap Access: No
Zoning: HMDR - Historic Medium Density Residential
Deed Restrictions: Unknown
Taxes: 14546.9
Tax Year: 2024
Pub Sewer HkUp: Yes
Street #: 1022
Street Name: Fleming
Street Suffix: Street
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Old Town - Unlisted (1.0)
Area: 02 - Key West
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: No
Control Depth: 0
Lot SqFt: 2724
Pool: Yes
Total Units: 2
Acres: 0.06
SqFt Source: Tax Records
Rentals Allowed: With Restrictions
Min Rental Days: 29
Floor Number: 2
Style: Duplex
Year Built: 1928
Living Apx SqFt: 2016
Total Bedrooms: 4
Full Baths: 2
Total Baths: 2
Remarks & Misc
Remarks – Consumer: Invest in Key West with this legal Duplex! Step into a piece of Key West history with this fully renovated, light-filled historic home in the heart of Old Town. Blending old-world charm with modern updates, this property offers easy living and generates income. Whether you're looking for a smart investment, a vacation getaway, or a new primary residence, this property is ready for you. Live in one unit and rent the other, or enjoy the entire home for yourself! There is an interior staircase to enter the upstairs unit.
Each spacious level features 2 bedrooms, 1 bathroom, a full kitchen with stainless steel appliances, laundry, and an open-concept living/kitchen/dining area. The lower unit opens to a deck and pool—perfect for relaxing and entertaining. The upper unit boasts abundant natural light and a large wraparound porch, ideal for enjoying the tropical surroundings. Both units come fully furnished, and the upstairs unit has a long-term tenant in place, ensuring immediate rental income.
Located in a prime spot close to the Old Seaport, top restaurants, and bars, but in a quieter neighborhood, this home is your ticket to island living in paradise!
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Fee Includes
None: 1
Dockage
None: 1
Tax Exemptions
None: 1
Appliances
Dryer: 1
Oven: 1
Range: 1
Refrigerator: 1
Stainless Steel Appliance(s): 1
Washer: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Ductless: 1
Heating
Ductless: 1
Waterfront
None: 1
Waterview
No Waterview: 1
Floor
Combo: 1
Tile: 1
Wood: 1
Neighborhood Feature
Bike Paths: 1
Interior Features
Built-in Cabinets: 1
Drapes/Blinds Incl: 1
Smoke Alarms: 1
Property Condition
Updated/Remodeled: 1
Building Style
Above Flood: Yes
Stories: 2 Stories
Windows/Doors
Double Hung Windows: 1
French Doors: 1
Wood Windows: 1
Security
On Premises System: 1
Secured Building: 1
Construction
Frame: 1
Land Size
Less Than 1/4 Acre: 1
Furnished
Furnished: 1
Terms
Cash: 1
Conventional: 1
Utilities
Elect Separate Meter: 1
FKAA: 1
Water Separate Meter: 1
Porch/Balcony
Deck: 1
Open Porch/Balcony: 1
Title
Negotiable: 1
Exterior Features
Fencing: 1
Pool Info
In Ground: 1
Concrete: 1
Pre-Wired
Cable: 1
Surround Sound: 1
Roof
Metal Roof: 1
Financial Status
Bank Owned: No
Potential Short Sale: No
Shutters
Panel: 1
Status Change Info
Status: Active
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: None
Waterview: No Waterview
Dockage: None
Property Condition: Updated/Remodeled
Furnished: Furnished
Cooling: Ceiling Fans(s); Ductless
Heating: Ductless
Utilities: Elect Separate Meter; FKAA; Water Separate Meter
Interior Features: Built-in Cabinets; Drapes/Blinds Incl; Smoke Alarms
Pre-Wired: Cable; Surround Sound
Appliances: Dryer; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer
Exterior Features: Fencing
Pool Info: In Ground; Concrete
Construction: Frame
Shutters: Panel
Floor: Combo; Tile; Wood
Roof: Metal Roof
Pets: Pets Allowed
Neighborhood Feature: Bike Paths
Security: On Premises System; Secured Building
Land Size: Less Than 1/4 Acre
Terms: Cash; Conventional
Title: Negotiable
Listing Office:
Ocean Sotheby's International Realty
Last Updated: October - 31 - 2025
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.